(3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸 | 64986-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸
• 英文名称: 7,12 diformate of cholic acid
• 英文别名: 7,12-diformylcholic acid；3α-hydroxy-7α,12α-diformyloxy-5β-cholan-24-oic acid；3a-Hydroxy-7a,12a-diformyloxy-5b-cholan-24-oic acid；(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diformyloxy-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 64986-86-3
• 化学式: C₂₆H₄₀O₇
• 分子量: 464.599
• InChiKey: DAKGJCRYZHTYJF-HZAMXZRMSA-N

物化性质

• 熔点：
  96-99 °C
• 沸点：
  589.9±50.0 °C(Predicted)
• 密度：
  1.21

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以92%的产率得到3-oxo-7α,12α-diformoxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Improved synthesis of 3-keto, 4-ene-3-keto, and 4,6-diene-3-keto bile acids

  摘要：

  Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80% yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups. The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60% yield, via bromination, dehydrobromination, and deformylation. By extending the dehydrobromination reaction, the 7 alpha-formoxyl group of the intermediate 4-ene-3-keto-7 alpha,12 alpha-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.

  DOI：

  10.1016/0039-128x(83)90087-9
• 作为产物：
  描述：

  cholic acid triformate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸
  参考文献：
  名称：

  The “triamino-analogue” of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry

  摘要：

  胆酸1已被转化为三胺5，具有全反式多环异胆酰基骨架和共同定向的轴向氨基基团；该体系的潜在支架作用通过转化为预组织的阴离子受体得到了展示。

  DOI：

  10.1039/b602415g

文献信息

• Synthesis of 3-glucuronides of unconjugated and conjugated bile acids.
  作者：JUNICHI GOTO、KAZUHIKO SUZAKI、TOSHIO NAMBARA

  DOI：10.1248/cpb.28.1258

  日期：——

  The 3-glucuronides of unconjugated, glyco- and tauro-conjugated bile acids have been prepared by an unequivocal route. Among three synthetic routes leading to the desired compounds, a method involving glucuronidation of the p-nitrophenyl ester by means of the Koenigs-Knorr reaction and subsequent conversion of the activated ester into the glyco-and tauro-conjugates was found to be most suitable. The nuclear magnetic resonance spectral data for bile acid glucuronides and related compounds are tabulated.

  非结合胆汁酸、糖结合胆汁酸和牛磺结合胆汁酸的 3-葡萄糖醛酸苷是通过一种明确的途径制备出来的。在获得所需化合物的三种合成路线中，通过柯尼希斯-克诺尔（Koenigs-Knorr）反应对硝基苯酯进行葡萄糖醛酸化，然后将活化的酯转化为糖型和牛磺酸型共轭物的方法最为合适。胆汁酸葡萄糖醛酸和相关化合物的核磁共振光谱数据已列表。
• Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring
  作者：Tomasz Pospieszny、Izabela Małecka、Zdzisław Paryzek

  DOI：10.1016/j.tetlet.2011.11.027

  日期：2012.1

  A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3 alpha-azidoacetoxy-7 alpha,12 alpha-diformyloxy-5 beta-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (H-1 NMR, C-13 NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs). (C) 2011 Elsevier Ltd. All rights reserved.
• Zhu, Xingpei; Amouzou, Etchri; McLean, Stewart, Canadian Journal of Chemistry, 1987, vol. 65, p. 2447 - 2449
  作者：Zhu, Xingpei、Amouzou, Etchri、McLean, Stewart

  DOI：——

  日期：——
• KRAMER, WERNER;SCHNEIDER, STEPHAN, J. LIPID RES., 30,(1989) N, C. 1281-1288
  作者：KRAMER, WERNER、SCHNEIDER, STEPHAN

  DOI：——

  日期：——
• ZHU, XINGPEI;AMOUZOU, ETCHRI;MCLEAN, STEWART, CAN. J. CHEM., 65,(1987) N 10, 2447-2449
  作者：ZHU, XINGPEI、AMOUZOU, ETCHRI、MCLEAN, STEWART

  DOI：——

  日期：——